What should you take with you on your quickly approaching summer holiday? Well, as little as possible, meaning just one watch to do everything you do on a vacation. “Travel light, easy, and carefree” is my motto. Picking the best summer watches at three different price points to accompany me on my vacation is a mostly hypothetical exercise. Still, I managed to select one practical watch under $1,000, another under $10,000, and an unlimited-budget option, with the last two being the hypothetical ones. Although I might not wear the two more costly picks on my upcoming summer trip, I still chose them based on hands-on personal experience.Don't race what you can't replace. The same principle applies to vacation watches if you ask me. I always stay realistic when picking the one watch I’ll take with me to go swimming, riding, dining, drinking, lounging, etc. Full disclosure: I always take a watch in the sub-$1,000 category. But that doesn't mean I can't form a thought about vacation watches that are far more costly. The watches I picked in the sub-$10,000 and money-is-no-issue categories made it onto the list because I had the pleasure of experiencing and wearing them in real life. I wore the sub-$10,000 Tudor in harsh and tough conditions and the sky-is-the-limit Patek Philippe in far more relaxed circumstances.The best summer watches Sub-$1,000: Casio G-Shock GA-B2100C-9AIt's as bright as the Sun, and just like the star our planet spins around, it will rise in the morning. I'm talking about the Casio G-Shock GA-B2100C-9A ($159), the striking yellow CasiOak that survived a tough-testing session last year. From a functional perspective, you can't go wrong by taking this watch on a summer vacation. The G-Shock GA-B2100C-9A has practical functions, including world time, alarms, and a stopwatch. Plus, with its solid build and 200m depth rating, this watch is certainly appropriate for summer activities. The high-quality resin that Casio uses feels great and keeps the total weight down to just 52 grams for a comfortable wearing experience. It’s also comforting to know that the 45.4mm 48.5 11.9mm watch case is reinforced with carbon (Casio’s Carbon Core Guard). Additionally, there’s strong mineral glass over the dial, revealing analog hands and a small diamond-shaped display for digital functions.As you can see in the pictures, this CasiOak shows some battle scars. It has a unique look you could call “accidental” or “random custom.” I know how it happened. I was there. I’m also responsible for how the watch looks today, which has created a bond between us. When I take the solar-powered, Bluetooth-equipped GA-B2100C-9A with me on my vacation, we will experience new adventures, and our bond will probably become tighter.Sub-$10,000:?Tudor Pelagos FXD Chrono Cycling EditionThere's one thing I know: the Tudor Pelagos FXD Chrono Cycling Edition ($5,390) wouldn’t waver if I took it on vacation. It can take anything you throw at it and look good while taking a beating. I write this confidently because I wore this watch while riding the Chasing Cancellara bike race in challenging conditions. The chronograph dealt with large amounts of rainwater. Its 100m-water-resistant, 43 13.2mm featherweight carbon composite case with a titanium back proved very comfortable too. Its lightness made me forget I was wearing a watch when not looking at it. The single-pass fabric strap always felt comfortable and secure, contributing to the watch’s excellent wearability. Importantly, the high-contrast black dial and large white Snowflake hands made the watch easy to read in murky conditions as well.Yes, Tudor made a functional watch, but its dark looks are without gimmicky details, making it a stylish companion for summer. With its fabric strap and bold aesthetic, this Pelagos FXD Chrono “Cycling Edition” looks best with casual attire in a relaxed setting. Sure, it would look good while enjoying an aperitif on a terrace, but I’d probably just want to take it riding all the time.Money is no issue: Patek Philippe Nautilus 5980/1A-001Because we're now in the category where money is no issue, why should I bother telling you that when the Nautilus 5980/1A-001 cost around $25,000, it was considered rather expensive for a steel chronograph with an odd, not very Patek-ish dial design? There's also no point in telling you that the once-unloved chronograph now goes for an average price of around $100,000?on?Chrono24. Instead, I will tell you that this blue-dial chronograph introduced in 2006 and discontinued in 2014 looks like a million bucks on the wrist.I think the ref. 5980/1 does the impossible: it makes a chronograph complication look good in an iconic watch. Imagine two or even three sub-dials on a Nautilus’s horizontally embossed blue dial. That would result in a distorted and cluttered look. The single chronograph sub-dial at 6 o'clock, however, makes sense. The two concentric circles that display the elapsed minutes and hours elevate the classic Nautilus to a complicated athlete.The steel 40.5 12.2mm case is water resistant to 120 meters and shows a distinct bezel featuring a brushed top and high-polished edges. The combination of the “winged” case shape, rounded octagonal bezel, and the high level of finishing makes this ultra-sports watch a desirable looker. But it’s not just handsome on the outside. The sapphire window of the exhibition case back allows a nice view of the exquisitely finished Patek Philippe caliber CH 28?520 C outfitted with a 21K gold central rotor, a Breguet-overcoil hairspring, and a four-arm Gyromax balance.Playing with your Nautilus 5980/1A-001 while overlooking the ocean will be a most satisfying, zen-like experience. How the 4Hz caliber CH 28?520 C functions and feels under the fingers when operating the pushers is phenomenal, crisp, precise, and ever so subtle.Choosing the best summer watches: which watch would you wear?Putting this eclectic shortlist together sure was a fun exercise. Please let me know your thoughts on the three summer watches I picked. Which one would you wear? Enjoy your summer, everyone, whatever it has in store for you.